New York detective Ichabod Crane is sent to Sleepy Hollow to investigate a series of mysterious deaths in which the victims are found beheaded.
I feel pretty confident that FYA readers are familiar with 1) the Washington Irving story The Legend of Sleepy Hollow and 2) Tim Burton. Put these together, and you get a campy, classic tale retold with the signature gothic quirk of Halloween’s favorite director. We all know the story, but it’s Tim Burton’s vision combined with an all-star cast that keeps this movie at the top of my October must-watch list year after year.
Johnny Depp as Ichabod Crane
Depp plays the famously squeamish Crane with just enough effiminacy and physical humor that it makes you wonder if this was the beginning of his Jack Sparrow character bubbling to the surface. Also, one could argue that this movie marked the end of Depp’s rise to heartthrob status and the beginning of his slow, sad decent into pirate troll person. Enjoy it: he’s never this hot again.
Christina Ricci as Katrina Van Tassel
Katrina is a bit demure for a Christina Ricci character, but it was post-colonial New England, and it is a Tim Burton film. She’s haunting with her long blonde locks and pale skin and eyebrows.
Michael Gambon as Baltus Van Tassel
Our dearest Dumbledore is almost unrecognizable…until he opens his mouth. There’s no hiding that wizardy tenor.
Christopher Walken as the Headless Horseman
One of Hollywood’s most famous voices playing an uncredited role with zero speaking parts. And yet, it’s perfect.
Miranda Richardson as Lady Van Tassel
A role only slightly more ominous than her HP alter ego, Rita Skeeter.
Richard Griffiths as Magistrate Philipse
The fact that this movie came out in 1999 and the first Harry Potter movie didn’t come out until 2001 makes this cast all the more delightful.
Couch-Sharing Capability: Summon Thy Significant Other
Husband, girlfriend, Tinder date – you’re going to need someone you feel comfortable snuggling up to, because this movie offers up its fair share of spooks. Plus, it’s got that whole post-colonial-New England-in-the-autumn thing that makes you want to get cozy under a plaid blanket while drinking cider.
Recommended Level of Inebriation: Spiked Cider
Speaking of cider, pour a butt-load of whiskey into yours, because you’re gonna need to be a little drunk to get past the fact that sentient leather dreamcatcher/poster child for Not Aging Well Johnny Depp stars in this one. This was my favorite movie in high school, when JD was at peak hotness and before I knew that he was a garbage human, so it requires a half cup of the hard stuff for me to enjoy it like I used to.
Use of Your Streaming Subscription: Halloween Prep
No one – I repeat, NOT A SINGLE SOLITARY SOUL – does non-horror Halloween like Tim Burton. If you want to get into the Halloween spirit (you do) but don’t feel like watching another yawn-inducing slasher flick (you don’t), Sleepy Hollow is the perfect combination of creepy crawly Halloween vibes and the aformentioned colonial-New England-autumnal vibes. It’s, like, October in movie form.